2-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide → HCID 178448691, compound

HRID 729277Notes

Reaction equation

HRID 729277 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4].[NH2:20][C:21]1[N:25]=[CH:24][NH:23][N:22]=1>CN(C=O)C>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:20][C:21]2[N:25]=[CH:24][NH:23][N:22]=2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxideHCID 178418311HCID 178418311, compound

Product 1

HCID 178448691HCID 178448691, compoundYield 3.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.110 g, 0.33 mmol) and 3-amino-1,2,4-triazole (0.083 g, 0.991 mmol) in DMF (0.5 mL) was heated at 140° C. for 25 mins in a microwave reactor. The residue was purified by preparative HPLC (Column Ace C8 (5u), 0.1M NH4OAc/MeCN, gradient) to give the title compound (0.0036 g, 2.2%); 1H-NMR (500 MHz, CD3CN): δ 7.78 (s, 1H), 7.20-7.40 (m, 5H), 3.74 (t, 2H), 1.84-1.76 (m, 2H), 1.51-1.42 (m, 2H), 0.99 (t, 3H); Mass Spectrum: M+H 348.

Workup

  1. customThe residue was purified by preparative HPLC (Column Ace C8 (5u), 0.1M NH4OAc/MeCN, gradient)

Sources & evidence

ORD record
ord-1852d94f43804a9a8900e96cbfedb470
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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